Heretofore, bis(aminomethyl)cyclohexanes have been well known for a raw material of polyamide used for fiber, film, etc. Also, bis(isocyanatomethyl)cyclohexanes derived from bis(aminomethyl)cyclohexanes are useful as a raw material of polyurethane used for, for example, paints, adhesives, plastic lenses, etc.
As a method for producing such bis(aminomethyl)cyclohexanes, for example, Patent Document 1 below has proposed a method for producing bis(aminomethyl)cyclohexanes by nuclear hydrogenation (hydrogen addition to aromatic rings) of xylylenediamine in the presence of, for example, a ruthenium catalyst using one or more solvents selected from alkylamines and alkylenediamines.
As a method for producing xylylenediamine used in the above-described method, for example, Patent Document 2 has proposed ammoxidation of xylene using a metal oxide catalyst such as vanadium to produce phthalonitrile, and then hydrogenation of the phthalonitrile in the presence of a nickel catalyst.
Patent Document 3 below has proposed a method for producing bis(aminomethyl)cyclohexanes in which hydrogen cyanide is added to 4-cyanocyclohexene to produce dicyanocyclohexanes, and then the dicyanocyclohexanes are hydrogenated in the presence of a catalyst.
Furthermore, as a method for producing bis(aminomethyl)cyclohexane, for example, Non-Patent Document 1 (Malachowski et al.) discloses the following: an acid chloride derivative is prepared using cyclohexanedicarboxylic acid with thionyl chloride; cyclohexane diamide is prepared using the acid chloride derivative with ammonia; and thereafter, the cyclohexane diamide is further allowed to react with thionyl chloride to obtain dicyanocyclohexane, and then the obtained dicyanocyclohexane is hydrogenated.